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Book Review Fascinating Alchemical HistoryЧA Labor of Love Nucleophilic Aromatic Substitution of Hydrogen. By O. N. Chupakhin V. N. Charushin and H. C

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Fascinating Alchemical History-A
Nucleophilic Aromatic Substitution of
Hydrogen. By 0. N . Chupakliin, V. N .
Cliarid~itia n d H . C. van clrr Plus.
Academic Press, San Diego, 1994.
367 pp.. hardcover $95.00.--ISBN
0-12-1 74640-2
The chemistry of aromatic compounds
i s presently not in the mainstream of or-
ganic chemistry research. although a substantial proportion of the products of the
fine chemicals iiidustry contain aromatic
moieties. and there are still many challenging and important questions concerning reactions of aromatic compounds.
Therefore the monograph Nucleophilic
Aronirilic, Sirh.~/i/u/ionof Hydrogen by
0. N . Chupukhin. V. N. Charushin. and
H . C. vaii der Plas is a very welcome and
needed contribution.
The book is divided into four chapters:
1. Introduction (16 pp.), 2. Nucleophilic
Substitution of Hydrogen in Arenes
(70 pp.). 3. Nucleophilic Substitution of
Hydrogen in Heteroaromatics ( 1 52 pp.),
und 4. Reactivity of Arenes and Heteroareiies and Mechanisms of the SE Reactions (40 pp.). The length of the third
chapter. which forms more than half of
the book, rctlects the personal interest of
the authors who are very active in the
chemistry of‘ mines. In the first chapter
the authors formulate the theme of the
book. present basic concepts o f the reactions between nucleophilic agents and
electrophilic arenes. and briefly discuss
possible w a q s in which the 0’’ adducts of
nucleophilic agents to electrophilic arenes
can be converted into products. In the second chapter these possibilities are discussed iii detail for the reactions of nucleophiles with carbocyclic nitroarenes
and complexes of arenes with transition
Thir wc11o11cotit:iins hook review? .ind a list of
iit‘i+hiioA\ i-ccel\ed by theeditor. Book revie\&sarc
i w i t ten hy I n i I 1‘1 ti on from the editor. Suggestions
I b r honk\ I O lhc reviened and for hook reviewers
i i i c \\elconic Puhli\hcrs should send brochures or
(hcrtcr) hook\ 10 Dr Kalf Baumann. Kedaktion
Angcv.:iiidIc C l i ~ n i i e .Poalkich 1 0 1 161. D-69451
Wetnhcnn. i edcriil Kcpublic ofGerm;inq The edit o i - r c s c r b e tlic right of selecting which books uill
he ievic\vcd Ilninvited hooks iiot chosen for
re\ic\\ UIII not he rektrned.
Labor of Love
metals. The third and longest chapter describes analogous reactions with electrophilic heteroarenes. This is mostly
devoted to the various possibilities of
nucleophilic amination, mainly the
Chichibabin reaction- particularly its oxidative variant. The fourth chapter deals
with mechanistic aspects of the nucleophilic substitution of hydrogen, foi-mation of the oHadducts, and their conversion to the final products.
The book is well written and also contains examples of experimental procedures. It will be of great value to chemists
working in research laboratories in
academia and industry who need to be
acquainted with possibilities o f introducing substituents into aromatic rings via
this process. The experimental procedures
enable the reader to evaluate the practical
usefulness of a variety of reactions without the necessity to consult the original
literature. An additional advantage of this
book. written partly by Russian chemists,
is that it contains many references to the
Russian literature. often not available in
Western libraries and therefore somewhat
I also have some critical remarks about
this book. First of all, in promoting the
usefulness of nucleophilic substitution of
hydrogen the authors should stress in a
more unambiguous way that where there
is competition from the S,Ar reaction of
halogen this is just a secondary process.
Also it seems that sigmatropic rearrangement reactions such as the Hauser-Sommelet rearrangement or the Gassmann
reaction, which are included in the book.
are close analogs of the Claisen aryl-ally1
ethers rearrangement and should not be
considered as the nucleophilic substitution of hydrogen. Also nucleophilic aromatic substitutions via arynes can hardly
be considered as examples of nucleophilic
substitution of hydrogen. The titles of the
chapters are somewhat inconsistent because the general term “arenes” also embraces “heteroarenes”. In the list of contents the title of Chapter 4 should be
”Heteroarenes”. not “Hetarenes”. The
mechanistic discussions in Chapter 4 are
sometimes superficial. There are some
rather questionable opinions: for example. orientation effects in nucleophilic
addition to derivatives of nitrothiophene,
nitrofuran. etc. (p. 256) should be explained as due to efficient conjugation,
not as an anomeric effect. Also the preceding discussion concerning site selectivity (p. 255) appears doubtful. There is only
a subject index, which is not sufficiently
comprehensive. These minor flaws do not
spoil my general positive impression of
the book, which due to its great value
should find a place not only in libraries
but also in individual collections.
M i c c ~,.slu
II’ M$
Institute of Orpanic Chemistry
Polish Academy of Sciences
Warsaw (Poland)
The Jewish Alchemists. A History and
Source Book. By R. Piitai. Princeton
University Press, Princeton. NJ, 1994.
XVI, 617 pp., hardcover $35.00.ISBN 0-691-03290-4
When I taught Sunday School at
Fresno’s Temple Beth Israel during the
late 1950s and early 1960s. the consensus
was that mysticism had never occupied
more than a minor position in Judaism.
This denigration of the Zohar and the
Kabbalah was probably due to the earlier
influence of the Jewish Enlightenment
(Haskalah) and its attempt to distance Judaism from “unenlightened” superstition.
Similarly, as Professor Raphael Patai, the
eminent Hungarian-born octogenarian
Jewish anthropologist. folklorist, Biblical
scholar, and prolific author. points out,
contemporary Jewish scholars have asserted that the participation of Jews in
alchemy was likewise insignificant. Although there exists n o inventory of alchemical manuscripts written by Jews,
nor even a study o f references to alchemy
found in books written by Jews, and although the number of Jewish alchemists
was small in comparison to the number o f
non-Jewish alchemists i n the countries of
the Jewish Diaspora. Jewish alchemists
exerted an important influence on the
origin, development. transmission, and
spread of alchemy.
In fact, as Professor Patai’s book effectively demonstrates. throughout much of
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